Phosphorus oxychloride → 4-Chloro-8-iodoquinoline

HRID 1958451Notes

Reaction equation

HRID 1958451 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[CH:8][C:7]2=O.O=P(Cl)(Cl)[Cl:15]>CN(C=O)C>[Cl:15][C:7]1[C:6]2[C:11](=[C:2]([I:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 124036904-Hydroxy-8-iodoquinoline

Product 1

HCID 124036924-Chloro-8-iodoquinolineYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Iodo-1H-quinolin-4-one (3.36 g, 8.72 mmol) was suspended in POCl3 (8 mL, 87.2 mmol) and catalytic anhydrous DMF (6.72 μL) was added. The mixture was refluxed for 1 h. The hot crude was poured over ice and the mixture stirred until ice was completely melted. Solid was filtered off, thoroughly washed with water and kept in the vacuum oven overnight to afford 4-chloro-8-iodo-quinoline as a grayish solid (2.47 g, 98%). 1H NMR (DMSO-d6, 400 MHz) δ 7.45 (t, 1H), 7.81 (d, 1H), 8.19 (dd, 1H), 8.45 (dd, 1H), 8.87 (d, 1H). Exact mass calculated for C9H5ClIN 288.92, found 289.9 (MH+).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. additionThe hot crude was poured over ice
  3. filtrationSolid was filtered off
  4. washthoroughly washed with water
  5. customkept in the vacuum oven overnight

Sources & evidence

ORD record
ord-5e4cc2e3cdbc461c9fa4be10ee809330
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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